Photolabile protection of 1,2- and 1,3-diols with salicylaldehyde derivatives.
1,2- and 1,3-diols, including carbohydrates, can be readily caged as acetals of 5-methoxy- or 5-hydroxysalicylaldehydes. Irradiation of these acetals with 300 nm light results in their efficient (Phi = 0.2-0.3) cleavage, regenerating an aldehyde and a glycol in excellent chemical yield. Photoreactive 5-hydroxysalicylaldehyde acetals can be produced by mild in situ reduction of photostable p-quinone precursors.
Kostikov
Alexey P
AP
Department of Chemistry, University of Georgia, Athens, Georgia 30602, USA.
Popik
Vladimir V
VV
D000080:Acetals / Q000737:chemistry; D000438:Alcohols / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D010777:Photochemistry
D000080:Acetals; D000438:Alcohols; D000447:Aldehydes; C013243:salicylaldehyde